LEWIS ACID-CATALYZED REARRANGEMENTS OF MYOINOSITOL ORTHOFORMATE DERIVATIVES

被引：38
|
作者：
GILBERT, IH
HOLMES, AB
PESTCHANKER, MJ
YOUNG, RC
机构：
[1] UNIV CAMBRIDGE,CHEM LAB,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND
[2] SMITHKLINE BEECHAM RES LTD,WELWYN GARDEN CIT AL6 9AR,HERTS,ENGLAND
来源：
CARBOHYDRATE RESEARCH | 1992年 / 234卷
关键词：
D O I：
10.1016/0008-6215(92)85043-Y
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Reduction of 2,4,6-tri-O-benzyl-DL-myo-inositol 1,3,5-orthoformate (1) With di isobytylaluminium hydride gave 2,4,6-tri-O-benzyl-1,3-O-methylene-DL-myo-inositol (2), whereas reaction with trimethylaluminium gave 2,4,6-tri-O-benzyl-1,5-O-ethylidene-DL-myo-inositol (6). 2,4,5,6-Tetra-O-benzyl-1,3-O-methylene-DL-myo-inositol (16) reacted with allyltrimethylsilane in the presence of Lewis acids to give 2,4,5,6-tetra-0-benzyl-1-O-(3-butenyl)-DL-myo-inositol [(+/-)-17] or rearranged to give 4,5,6-tri-O-benzyl-1,2-0-methylene-DL-myo-inositol [+/-)-18].
引用
收藏
页码：117 / 130
页数：14
相关论文
共 50 条
  • [1] LEWIS ACID-CATALYZED REARRANGEMENTS OF NITROXIDE RADICALS
    CAZIANIS, CT
    EATON, DR
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (13): : 2463 - 2470
  • [2] Recent Advances on the Lewis Acid-Catalyzed Cascade Rearrangements of Propargylic Alcohols and Their Derivatives
    Zhu, Yuanxun
    Sun, Lang
    Lu, Ping
    Wang, Yanguang
    ACS CATALYSIS, 2014, 4 (06): : 1911 - 1925
  • [3] ACID-CATALYZED CATIONIC REARRANGEMENTS OF DIHYDROBENZOFURANE DERIVATIVES
    KOZAK, J
    KOZERSKI, L
    BULLETIN OF THE POLISH ACADEMY OF SCIENCES-CHEMISTRY, 1985, 33 (9-10): : 421 - 426
  • [4] ACID-CATALYZED REARRANGEMENTS OF TRICYCLO[4.3.2]PROPELLANE DERIVATIVES
    SMITH, AB
    WEXLER, BA
    TETRAHEDRON LETTERS, 1984, 25 (22) : 2317 - 2320
  • [5] ACID-CATALYZED REACTION OF ACETYLFERROCENE WITH TRIETHYL ORTHOFORMATE
    SASAKI, Y
    PITTMAN, CU
    JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (21): : 3723 - 3726
  • [6] ACID-CATALYZED REARRANGEMENTS OF 7-OXYGENATED NORBORNENYL DERIVATIVES
    JONES, VK
    JONES, LB
    TETRAHEDRON LETTERS, 1970, (36) : 3171 - &
  • [7] ACID-CATALYZED REARRANGEMENTS OF HUMULENE
    DAUBEN, WG
    HUBBELL, JP
    VIETMEYER, ND
    JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (04): : 479 - 485
  • [8] ACID-CATALYZED REARRANGEMENTS OF CYCLOBUTANONES
    ERMAN, WF
    TREPTOW, RS
    BAKUZIS, P
    WENKERT, E
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (03) : 657 - &
  • [9] ACID-CATALYZED REARRANGEMENTS OF POLYMETHYLNAPHTHALENES
    OKU, A
    YUZEN, Y
    JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (26): : 3850 - 3857
  • [10] ACID-CATALYZED REARRANGEMENTS OF MONOTHIOACETALS
    HAGEN, JP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 42 - ORGN
12345